JP6225358B2 - ２−アミノ置換ベンズアルデヒド化合物を製造する方法 - Google Patents
２−アミノ置換ベンズアルデヒド化合物を製造する方法 Download PDFInfo
- Publication number
- JP6225358B2 JP6225358B2 JP2016546566A JP2016546566A JP6225358B2 JP 6225358 B2 JP6225358 B2 JP 6225358B2 JP 2016546566 A JP2016546566 A JP 2016546566A JP 2016546566 A JP2016546566 A JP 2016546566A JP 6225358 B2 JP6225358 B2 JP 6225358B2
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- Japan
- Prior art keywords
- group
- hydrogen atom
- bonded
- benzaldehyde
- halogeno
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 150000003935 benzaldehydes Chemical class 0.000 title claims description 39
- 238000000034 method Methods 0.000 title description 14
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 title description 3
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 47
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 45
- 125000005843 halogen group Chemical group 0.000 claims description 43
- 125000003545 alkoxy group Chemical group 0.000 claims description 39
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 36
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 32
- 238000006243 chemical reaction Methods 0.000 claims description 31
- 125000000217 alkyl group Chemical group 0.000 claims description 28
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 28
- 238000004519 manufacturing process Methods 0.000 claims description 26
- 150000001875 compounds Chemical class 0.000 claims description 21
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims description 18
- 238000010511 deprotection reaction Methods 0.000 claims description 11
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 9
- 125000003277 amino group Chemical group 0.000 claims description 8
- 238000006138 lithiation reaction Methods 0.000 claims description 8
- -1 benzaldehyde compound Chemical class 0.000 description 31
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 26
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 17
- 239000007788 liquid Substances 0.000 description 14
- 150000002009 diols Chemical class 0.000 description 13
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 12
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 0 *c(c(*)c1*)c(*)c(C=O)c1N Chemical compound *c(c(*)c1*)c(*)c(C=O)c1N 0.000 description 8
- 238000005160 1H NMR spectroscopy Methods 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 7
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- 238000005576 amination reaction Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000004445 quantitative analysis Methods 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- KFPRBQYQKRKHRR-UHFFFAOYSA-N 2-(2-azido-3,4-difluorophenyl)-1,3-dioxolane Chemical compound N(=[N+]=[N-])C1=C(C=CC(=C1F)F)C1OCCO1 KFPRBQYQKRKHRR-UHFFFAOYSA-N 0.000 description 4
- JDIKHNSLOQHKLX-UHFFFAOYSA-N 2-(3,4-difluorophenyl)-1,3-dioxolane Chemical compound C1=C(F)C(F)=CC=C1C1OCCO1 JDIKHNSLOQHKLX-UHFFFAOYSA-N 0.000 description 4
- LBLKQHXUONTWAP-UHFFFAOYSA-N 6-(1,3-dioxolan-2-yl)-2,3-difluoroaniline Chemical compound O1C(OCC1)C1=CC=C(C(=C1N)F)F LBLKQHXUONTWAP-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 239000003638 chemical reducing agent Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 229910052763 palladium Inorganic materials 0.000 description 4
- NDLIRBZKZSDGSO-UHFFFAOYSA-N tosyl azide Chemical compound CC1=CC=C(S(=O)(=O)[N-][N+]#N)C=C1 NDLIRBZKZSDGSO-UHFFFAOYSA-N 0.000 description 4
- GOYDNIKZWGIXJT-UHFFFAOYSA-N 1,2-difluorobenzene Chemical compound FC1=CC=CC=C1F GOYDNIKZWGIXJT-UHFFFAOYSA-N 0.000 description 3
- IYSSZOLMHLGBSU-UHFFFAOYSA-N 2-amino-3,4-difluorobenzaldehyde Chemical compound NC1=C(C=O)C=CC(=C1F)F IYSSZOLMHLGBSU-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 150000001540 azides Chemical class 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 238000006722 reduction reaction Methods 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 2
- 150000000180 1,2-diols Chemical class 0.000 description 2
- 150000000185 1,3-diols Chemical class 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- JPHKMYXKNKLNDF-UHFFFAOYSA-N 3,4-difluorobenzaldehyde Chemical compound FC1=CC=C(C=O)C=C1F JPHKMYXKNKLNDF-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 description 2
- 238000005885 boration reaction Methods 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 2
- 230000002441 reversible effect Effects 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- LZUMVTPOQOUWRQ-UHFFFAOYSA-N 1-(2-aminohydrazinyl)hexane Chemical compound CCCCCCNNN LZUMVTPOQOUWRQ-UHFFFAOYSA-N 0.000 description 1
- GDIYDPBHVKDDIR-UHFFFAOYSA-N 2-amino-3-methoxybenzaldehyde Chemical class COC1=CC=CC(C=O)=C1N GDIYDPBHVKDDIR-UHFFFAOYSA-N 0.000 description 1
- XXICUUMWAHBIBR-UHFFFAOYSA-N 2-amino-4-chloro-5-fluorobenzaldehyde Chemical compound NC1=CC(Cl)=C(F)C=C1C=O XXICUUMWAHBIBR-UHFFFAOYSA-N 0.000 description 1
- FXWFZIRWWNPPOV-UHFFFAOYSA-N 2-aminobenzaldehyde Chemical class NC1=CC=CC=C1C=O FXWFZIRWWNPPOV-UHFFFAOYSA-N 0.000 description 1
- VTGRVYJPIVZZGS-UHFFFAOYSA-N 4-(chloromethyl)-1,2-difluorobenzene Chemical compound FC1=CC=C(CCl)C=C1F VTGRVYJPIVZZGS-UHFFFAOYSA-N 0.000 description 1
- YMQPKONILWWJQG-UHFFFAOYSA-N 4-bromo-1,2-difluorobenzene Chemical compound FC1=CC=C(Br)C=C1F YMQPKONILWWJQG-UHFFFAOYSA-N 0.000 description 1
- WYMZXNRXRADFTH-UHFFFAOYSA-N 4-chloro-5-fluoro-2-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC(Cl)=C(F)C=C1C=O WYMZXNRXRADFTH-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- FFYKPMSZVZWKAN-UHFFFAOYSA-N NC1=C(C=O)C=CC(=C1F)F.NC1=C(C=O)C=CC(=C1F)F Chemical compound NC1=C(C=O)C=CC(=C1F)F.NC1=C(C=O)C=CC(=C1F)F FFYKPMSZVZWKAN-UHFFFAOYSA-N 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000007265 chloromethylation reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- YJMNLPRMBFMFDL-UHFFFAOYSA-N n-diazo-2-methylbenzenesulfonamide Chemical compound CC1=CC=CC=C1S(=O)(=O)N=[N+]=[N-] YJMNLPRMBFMFDL-UHFFFAOYSA-N 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002900 organolithium compounds Chemical class 0.000 description 1
- 125000001979 organolithium group Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- NQPHMXWPDCSHTE-UHFFFAOYSA-N trifluoromethanesulfonyl azide Chemical compound FC(F)(F)S(=O)(=O)N=[N+]=[N-] NQPHMXWPDCSHTE-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C223/00—Compounds containing amino and —CHO groups bound to the same carbon skeleton
- C07C223/06—Compounds containing amino and —CHO groups bound to the same carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C221/00—Preparation of compounds containing amino groups and doubly-bound oxygen atoms bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B51/00—Introduction of protecting groups or activating groups, not provided for in the preceding groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B61/00—Other general methods
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/16—Radicals substituted by halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/28—Radicals substituted by nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2014177563 | 2014-09-01 | ||
| JP2014177563 | 2014-09-01 | ||
| PCT/JP2015/073836 WO2016035609A1 (ja) | 2014-09-01 | 2015-08-25 | ２－アミノ置換ベンズアルデヒド化合物を製造する方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPWO2016035609A1 JPWO2016035609A1 (ja) | 2017-04-27 |
| JP6225358B2 true JP6225358B2 (ja) | 2017-11-08 |
Family
ID=55439675
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016546566A Active JP6225358B2 (ja) | 2014-09-01 | 2015-08-25 | ２−アミノ置換ベンズアルデヒド化合物を製造する方法 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US10047037B2 (ko) |
| EP (1) | EP3196189B1 (ko) |
| JP (1) | JP6225358B2 (ko) |
| KR (1) | KR101879143B1 (ko) |
| CN (1) | CN106573874B (ko) |
| WO (1) | WO2016035609A1 (ko) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113773204B (zh) * | 2021-10-20 | 2024-04-16 | 上海万溯药业有限公司 | 一种氟代苯胺的制备方法 |
| CN114230547A (zh) * | 2021-12-29 | 2022-03-25 | 江苏广域化学有限公司 | 取代苯甲醛缩醇的合成方法 |
| CN114409556B (zh) * | 2022-01-28 | 2024-10-18 | 兰州康鹏威耳化工有限公司 | 一种3,4-二取代-2-氨基苯甲醛的制备方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2306919A1 (de) | 1973-02-13 | 1974-08-15 | Bayer Ag | Verfahren zur herstellung von aminochlor-benzaldehyden |
| DE4142173A1 (de) | 1991-12-20 | 1993-06-24 | Basf Ag | Verfahren zur herstellung von 2-aminobenzaldehyden |
| JP3577775B2 (ja) | 1995-04-14 | 2004-10-13 | 宇部興産株式会社 | ４，５−ジハロアニリン誘導体およびその製造方法 |
| JP2000007627A (ja) | 1998-06-19 | 2000-01-11 | Tosoh Corp | ホルミルトリアリールアミンの製造方法 |
| JP2003503495A (ja) | 1999-06-30 | 2003-01-28 | アベンテイス・フアルマ・ソシエテ・アノニム | 新規なベンゾ［ｆ］ナフチリジン誘導体、それらの製造およびそれらを含む組成物 |
| TW200808739A (en) | 2006-04-06 | 2008-02-16 | Novartis Vaccines & Diagnostic | Quinazolines for PDK1 inhibition |
| CN103030568A (zh) | 2011-10-08 | 2013-04-10 | 侯召羽 | 氨基香兰素的合成工艺 |
| JP2013237648A (ja) | 2012-05-16 | 2013-11-28 | Mitsui Chemicals Agro Inc | ３−シアノキノリン誘導体の製造方法 |
-
2015
- 2015-08-25 WO PCT/JP2015/073836 patent/WO2016035609A1/ja active Application Filing
- 2015-08-25 KR KR1020177002258A patent/KR101879143B1/ko active IP Right Grant
- 2015-08-25 CN CN201580044966.8A patent/CN106573874B/zh active Active
- 2015-08-25 JP JP2016546566A patent/JP6225358B2/ja active Active
- 2015-08-25 EP EP15837423.1A patent/EP3196189B1/en active Active
- 2015-08-25 US US15/504,499 patent/US10047037B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| US20170226046A1 (en) | 2017-08-10 |
| CN106573874B (zh) | 2018-06-12 |
| JPWO2016035609A1 (ja) | 2017-04-27 |
| EP3196189B1 (en) | 2020-09-23 |
| EP3196189A4 (en) | 2018-01-24 |
| WO2016035609A1 (ja) | 2016-03-10 |
| CN106573874A (zh) | 2017-04-19 |
| EP3196189A1 (en) | 2017-07-26 |
| KR101879143B1 (ko) | 2018-07-16 |
| US10047037B2 (en) | 2018-08-14 |
| KR20170023158A (ko) | 2017-03-02 |
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